The present invention is related to novel intermediates which are useful in the preparation of certain piperidine derivatives which are useful as antihistamines, antiallergy agents and bronchodilators [U.S. Pat. No. 4,254,129, Mar. 3, 1981, U.S. Pat. No. 4,254,130, Mar. 3, 1981, U.S. Pat. No. 4,285,958, Apr. 25, 1981 and U.S. Pat. No. 4,550,116, Oct. 29, 1985].
These antihistaminic piperidine derivatives can be described by the following formula: ##STR2## wherein W represents --C(.dbd.O)-- or --CH(OH)--;
R.sub.1 represents hydrogen or hydroxy; PA1 R.sub.2 represents hydrogen; PA1 R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; PA1 n is an integer of from 1 to 5; PA1 m is an integer 0 or 1; PA1 R.sub.3 is --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; PA1 each of A is hydrogen or hydroxy; and PA1 pharmaceutically acceptable salts and individual optical isomers thereof, PA1 with the proviso that where R.sub.1 and R.sub.2 are taken together to form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 or where R.sub.1 represented hydroxy, m is an integer 0. PA1 R.sub.1 represents hydrogen or hydroxy; PA1 R.sub.2 represents hydrogen; or PA1 R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; PA1 n is an integer of from 1 to 5; PA1 m is an integer 0 or 1; PA1 R.sub.3 is --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; each of A is hydrogen or hydroxy; and PA1 pharmaceutically acceptable salts and individual optical isomers thereof, PA1 with the proviso that where R.sub.1 and R.sub.2 are taken together to form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 or where R.sub.1 represented hydroxy, m is an integer 0. PA1 R.sub.5 is H, --CH.sub.2 OD wherein D is hydrogen, acetate or benzoate, --CHO, Br, Cl, I, CN, --COOH, --COOalkyl or --CONR.sub.6 R.sub.7 wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched and R.sub.6 and R.sub.7 are each independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or R.sub.6 and R.sub.7 taken together with the nitrogen atom form a pyrrolidine, piperidine or morpholine, with the proviso that R.sub.6 and R.sub.7 cannot both be represented by C.sub.1 -C.sub.6 alkoxy. ##STR5## wherein A is a hydrogen or hydroxy; and PA1 R.sub.5 is H, Br, Cl, I, CN, --COOH, --COOalkyl or --CONR.sub.6 R.sub.7 wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched and R.sub.6 and R.sub.7 are each independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or R.sub.6 and R.sub.7 taken together with the nitrogen atom form a pyrrolidine, piperidine or morpholine, with the proviso that R.sub.6 and R.sub.7 cannot both be represented by C.sub.1 -C.sub.6 alkoxy. ##STR6## wherein A is a hydrogen or hydroxy; and PA1 R.sub.5 is H, Br, Cl, I, CN, --COOH, --COOalkyl or --CONR.sub.6 R.sub.7 wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched and R.sub.6 and R.sub.7 are each independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or R.sub.6 and R.sub.7 taken together with the nitrogen atom form a pyrrolidine, piperidine or morpholine, with the proviso that R.sub.6 and R.sub.7 cannot both be represented by C.sub.1 -C.sub.6 alkoxy. ##STR7## wherein Hal is Cl, Br or I; PA1 n is an integer of from 1 to 5; PA1 A is a hydrogen or hydroxy; and PA1 R.sub.5 is H, CH.sub.2 OD wherein D is hydrogen, acetate or benzoate, CHO, Br, Cl, I, CN, --COOH or --CONR.sub.6 R.sub.7 wherein R.sub.6 and R.sub.7 are each independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or R.sub.6 and R.sub.7 taken together with the nitrogen atom form a pyrrolidine, piperidine or morpholine, with the proviso that R.sub.6 and R.sub.7 cannot both be represented by C.sub.1 -C.sub.6 alkoxy. ##STR8## wherein Hal is Cl, Br or I; PA1 n is an integer of from 1 to 5; PA1 A is a hydrogen or hydroxy; and PA1 R.sub.5 is H, Br, Cl, I, CN, --COOH, --COOalkyl or --CONR.sub.6 R.sub.7 wherein the alkyl moiety has from 1 to 6 carbonatoms and is straight or branched and R.sub.6 and R.sub.7 are each independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or R.sub.6 and R.sub.7 taken together with the nitrogen atom form a pyrrolidine, piperidine or morpholine, with the proviso that R.sub.6 and R.sub.7 cannot both be represented by C.sub.1 -C.sub.6 alkoxy. ##STR9## wherein Hal is Cl, Br or I; PA1 n is an integer of from 1 to 5; PA1 A is a hydrogen or hydroxy; PA1 R.sub.5 is H, Br, Cl, I, CN, --COOH, --COOalkyl or --CONR.sub.6 R.sub.7 wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched and R.sub.6 and R.sub.7 are each independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or R.sub.6 and R.sub.7 taken together with the nitrogen atom form a pyrrolidine, piperidine or morpholine, with the proviso that R.sub.6 and R.sub.7 cannot both be represented by C.sub.1 -C.sub.6 alkoxy. ##STR10## wherein Hal is Cl, Br or I; PA1 n is an integer of from 1 to 5; and PA1 A is a hydrogen or hydroxy. ##STR11## wherein A is a hydrogen or hydroxy. ##STR12## wherein Hal is Cl, Br or I; PA1 n is an integer of from 1 to 5; PA1 A is a hydrogen or hydroxy; and PA1 R.sub.5 is H, CH.sub.2 OD wherein D is hydrogen, acetate or benzoate, CHO, Br, Cl, I, CN, --COOH, --COOalkyl or --CONR.sub.6 R.sub.7 wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched and R.sub.6 and R.sub.7 are each independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or R.sub.6 and R.sub.7 taken together with the nitrogen atom form a pyrrolidine, piperidine or morpholine, with the proviso that R.sub.6 and R.sub.7 cannot both be represented by C.sub.1 -C.sub.6 alkoxy; and PA1 R.sub.1 represents hydrogen or hydroxy; PA1 R.sub.2 represents hydrogen; or PA1 R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; PA1 n is an integer of from 1 to 5; PA1 m is an integer 0 or 1; PA1 R.sub.5 is H, Br, Cl, I, CN or --CONR.sub.6 R.sub.7 wherein R.sub.6 and R.sub.7 are each independently H, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy or R.sub.6 and R.sub.7 taken together with the nitrogen atom form a pyrrolidine, piperidine or morpholine, with the proviso that R.sub.6 and R.sub.7 cannot both be represented by C.sub.1 -C.sub.6 alkoxy; PA1 A is hydrogen or hydroxy; and PA1 pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R.sub.1 and R.sub.2 are taken together to form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 or where R.sub.1 represented hydroxy, m is an integer 0. PA1 R.sub.1 represents hydrogen or hydroxy; PA1 R.sub.2 represents hydrogen; or PA1 R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; PA1 n is an integer of from 1 to 5; PA1 m is an integer 0 or 1; PA1 R.sub.3 is --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; each of A is hydrogen or hydroxy; and PA1 pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R.sub.1 and R.sub.2 are taken together to form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 or where R.sub.1 represented hydroxy, m is an integer 0, comprising the steps of: PA1 R.sub.1 represents hydrogen or hydroxy; PA1 R.sub.2 represents hydrogen; or PA1 R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; PA1 n is an integer of from 1 to 5; PA1 m is an integer 0 or 1; PA1 each of A is hydrogen or hydroxy; and PA1 pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R.sub.1 and R.sub.2 are taken together to form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 or where R.sub.1 represented hydroxy, m is an integer 0, comprising the steps of: PA1 (c) reacting the .omega.'-halo-.alpha.'-keto-.alpha.,.alpha.-dimethylphenylacetic acid ester compound with a piperidine compound of the formula PA1 R.sub.1 represents hydrogen or hydroxy; PA1 R.sub.2 represents hydrogen; or PA1 R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; PA1 n is an integer 3; PA1 m is an integer 0 or 1; PA1 R.sub.3 is --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; PA1 each of A is hydrogen or hydroxy; and PA1 pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R.sub.1 and R.sub.2 are taken together to form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 or where R.sub.1 represented hydroxy, m is an integer 0, comprising the steps of: PA1 R.sub.1 represents hydrogen or hydroxy; PA1 R.sub.2 represents hydrogen; or PA1 R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; PA1 n is an integer of from 1 to 5; PA1 m is an integer 0 or 1; PA1 R.sub.3 is --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; PA1 each of A is hydrogen or hydroxy; and PA1 pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R.sub.1 and R.sub.2 are taken together to form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 or where R.sub.1 represented hydroxy, m is an integer 0, comprising the steps of: PA1 R.sub.1 represents hydrogen or hydroxy; PA1 R.sub.2 represents hydrogen; or PA1 R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; PA1 n is an integer of from 1 to 5; PA1 m is an integer 0 or 1; PA1 R.sub.3 is --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; PA1 each of A is hydrogen or hydroxy; and PA1 pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R.sub.1 and R.sub.2 are taken together to form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 or where R.sub.1 represented. hydroxy, m is an integer 0, comprising the steps of: PA1 R.sub.1 represents hydrogen or hydroxy; PA1 R.sub.2 represents hydrogen; or PA1 R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; PA1 n is an integer of from 1 to 5; PA1 m is an integer 0 or 1; PA1 R.sub.3 is --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; PA1 each of A is hydrogen or hydroxy; and PA1 pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R.sub.1 and R.sub.2 are taken together to form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 or where R.sub.1 represented hydroxy, m is an integer 0, comprising the steps of: